Aldehydes & Ketones Questions and Answers

An unknown compound is found to contain 40 0 carbon 6 7 hydrogen and 53 3 oxygen with a molecular mass of 60 0 g mol What is the molecular formula of the unknown compound

3 Determine the empirical formulas for compounds with the following percent compositions a 15 8 carbon and b 40 0 carbon 6 7 hydrogen and 53 3 oxygen 84 2 sulfur

A Na BM Harott MeoH write a mechanism for the reaction

Choose the major product formed in the following reaction A B C Compound a E Compound b Compound c D Compound d Compound e CO CH CO CH CO CH CO CH 150 C CO CH CO CH d CO CH CO CH

What is the particle behavior of Formaldehyde like O C

Which of the following is benzophenone O C6H5 CO C6H5 O CoHs CHO O C6H5 C6H4 OH C6H5 CO CH3

What is the major product for the following reaction a O CH Cl 78 b Meys HCHO

namme product of with LDA 3 3 dimethy butan 2 on CH CH CH Br and

When benzaldehyde is treated with sodium borohydride subsequent aqueous work up followed by the reaction with Jones reagent the resultant product is phenylethanol phenylacetic acid benzoic acid Phenol Joohel O

In the following flow chart P1 P2 P3 P4 represent appropriate products of the indicated step Which molecule is not among P1 P2 P3 and P4 O 1 NaBH 2 H 0 P1 OH OH OH Kotbu P2 MCPBA P3 1 PhBr Mg ether 2 H 0 P4

4 Draw the keto tautomer of each of the following enols 10 points OH LOH

What is the product of the following sequence of reactions Br S Mg ether to OH or 1 2 H 0 H CrO 4 Product

2 H CH3 CN CH CH NH HOH CH3CHO Acetaldimine intermediate in the above sequence can also be obtained by A Reduction of acetaldoxime in the presence of Na C H5 OH Your Answer B Oxidation of ethylamine in the presence of KMnQ Correct Answer Reduction of methyl isonitrile in the presence of LiAlH

5 Please assign the configuration to the Juan yuMNH2 04 amino acid 6 Please give the appropriate reagents to complete the ff Synthesis O

Design a synthesis of the target molecule shown from the starting materials given plus any other needed reagents You will need to use BOTH types of protecting groups we have learned about Show all synthetic steps including the product of each step No mechanism It will probably require at least 6 steps Br H

What is the major organic product obtained from the following sequence of reactions Br 1 Mg THF PCC 28 O 2 3 H3O

What is the major product of the reaction below O O OH OH OH OH OH OH 1 NaBH4 2 H O

How many signals in the H NMR spectrum should be observed for the following compound Cu ntas se ales en el espectro de RMN H deben ser observadas para el siguiente compues H3C O a 1 O b 3 H

3 methylcyclohexene 4 carboxaldehyde is formed from a Diels alder rxn Draw the two starting materials in the correct orientation to form this product O H

Which of the following formed are upon hydrolysis of compound 2 HO 18 OH O compound 2 d H HO OH OH OH H HO HO 85 55 55 HO IV OH

What s wrong with the following mechanism CH6 0 O The arrow is backwards H 0 O There is no leaving group so there should be no arrows O An arrow is also needed to indicate the loss of a leaving group O The arrow should be removing a proton from the alpha carbon

6 Which enolate is formed as the major product in the following reaction Circle the correct one LDA 1 1 equiv 78 C OLI O or 198

Show the retrosinthesis and the conditions for the following reaction OE

5 What reagents are necessary to perform the following reaction te A Br2 H3O B Br2 CH3COOH C Br2 1 equiv NaOH D None of the above Br Br

BONUS Provide a mechanism for the following rxn 5 points CI CH3ONa OCH3

4 Which of the following compounds is the most acidic Circle your answer het he H H H

c Provide the organic starting materials necessary to synthesize the following compound via a Robinson Annulation 7 points D

1 Which of the following compounds could be the product of a Michael reaction circle all possible answers ge she H

2 Which of the following compounds could NOT undergo a self aldol condensation circle all possible answers H

a Provide the organic starting material s necessary to synthesize the following compound via an aldol condensation 6 points

5 How many ml of 4M NaOH would it take to neutralize 120ml of 1M HCI 6 Draw the structural formula for 2 methyl 1 pentanal

Show how to make the following compound K OH

oc Provide the major organic product of the reaction below Y me Ly

Provide the major organic product of the reaction below Y O Ether O Alcohol O Ketone OR

Pick the reactant that will produce a secondary alcohol O A OB OC H 2 H 0 A secondary alcohol i s C D

i Y Product Select Product Select LAG 4 bit dit

Predict the minding mactant which when used in excess will make A CH Br B CH MgBr C CH CH MgBr D CH CH OH OC 1 M of

Predict the reagent OC Liv Al H Raney Mi B NORM DJ LIAM E Naod COM RAHM O NaOH

T Predict the product O Aldehyde O Ketone O Alcohol O No reaction

where appropriate If no reaction is anticipated write no reaction

Synthesize octanal starting with acetylene Show the retrosynthesis and synthesis with all reagents and products at each step

g 1 HO 2 DIBAH 3 H O OH H 1 PHCOCI AICI 2 Na Cr O7 H SO4 H O 1 LAH 2 H O 3 H O 1 BH 3 THF 2 t BuOK 3 CH31

ed mechanism for the following write down adetailed mechani

7 Circle and name the functional groups in the following molecule 12 Stike H

Using the minimum steps of chemical reaction show how you would synthesize the following compounds The synthesis may involve more than one step Suggest suitable reagents solvents and structure of intermediates a 0 X ne b c d OH Br 2 4 OH NO OH it HO OH

3 NaOEt 4 t BuOK 5 H Pt 6 H Lindlar s catalyst 7 Na NH3 8 LAH or xs LAH then H O 9 NaBH CH OH 10 NaBH CN pH 5 Grignard Wittig and Gilman Reagents Assume then H O is included if a protonation step is needed MeMgBr EtMgBr PhMgBr PhCH MgBr G1 G2 G3 G4 Ph Me Culi Et Culi Ph Culi PhCH Culi G6 CH OH PhyP CH W1 G7 TT CI then H O NaOH 14 Hg OAc H O then NaBH 15 03 then Zn HCI or DMS 16 MCPBA or CH CO3H 17 Br light or NBS heat 18 HBr 19 HBr ROOR 20 PBr3 G8 COH K Ph P CHCH PhP CHCO Et Ph P CHPh W2 W3 W4 OH G9 13 UU CHX D E F A B C Alcohols Assume an acid catalyst H or pyridine is present if needed OH G5 G10 PH Reactant reagent List For Final Exam Enter code or letter in the appropriate boxes Note Exam responses are case insensitive Alkyl Halides X Cl Br or I Assume AICI is present if needed MgBr UV S T U V W Acid Chlorides Assume AICI or pyridine is present if needed OH N 24 SOCI pyridine 25 HNO3 H SO4 26 fuming H SO4 27 Fe HCl then NaOH 28 Zn Hg HCI 29 KCN or KCN PHCN 30 CO then H O 31 TH H HH AA BB CC GG DD EE FF Ketones Aldehydes and Epoxides Assume then H O is included if a protonation step is needed ww 32 NH 1 or 2 equiv 33 CH3NH 1 or 2 equiv 34 CH NH 1 or 2 equiv 35 EtNH 1 or 2 equiv 36 PhCH NH 1 or 2 equiv 37 LDA 78 C 38 NaH 25 C OH 39 LIAI OR H then H O 40 DIBAH then H O 41 Br H O 42 Br NaOH OH H O G OH XX A X Z 4 L H 47 CUCN 48 HBF4 49 H O heat 50 H PO 51 52 LOH Lo Len H2 HH2 ZZ OH R NH

Br H Draw the curved arrow mechanism for the reaction between the aldehyde and propyl bromide including the final product Be sure to include nonzero formal charges and lone pair electrons on all appropriate atoms Draw the resonance structure of the enolate ion only Do NOT include curved arrows in this box need help with 3rd box only thx

what is a possible mechanism for the transformation OEt OEt

NAME IN PeopleSoft Number Match the entries Proton numbering in column 1 with the entries Chemical shift column 2 and the entries splitting pattern in column 3 for the following molecule in NMR 6 Column 1 C1 C2 C4 C5 LETTERS C Column 2 2 41 1 07 4 01 1 21 S C2 C4 Column 3 Quartet Triplet Triplet Quartet C5

What is the expected product B for the following transformation O O H3C OEt 1 NaOEt EtOH 2 Mel A 1 NaOH A 2 H3O A